29

Oregon, WI Homes for Sale under $500,000

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  • 507 Janesville St, Oregon, WI 53575
    507 Janesville St, Oregon, WI 53575
    507 Janesville St, Oregon, WI 53575
    /62

    $365,000

    $25K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,728 Sq Ft

    507 Janesville St, Oregon, WI 53575

    This beautifully updated home offers a fully remodeled main level with a modern kitchen featuring custom granite countertops, hickory cabinets, a stylish full bath with tiled shower, and a welcoming entry porch with cathedral ceiling. A expansive 33'6"x22'6" garage fully insulated and sheet rocked and painted. The garage and second floor were added in 2015, 2016 and includes two bedrooms and a

    Agent Photo

    Steve Evers

    Great Rock Realty LLC

    507 Janesville St, Oregon, WI 53575
  • 5 Acres Lincoln Rd, Oregon, WI 53575
    5 Acres Lincoln Rd, Oregon, WI 53575
    5 Acres Lincoln Rd, Oregon, WI 53575
    /23

    $499,900

    • Land
    • 5.01 Acres
    • $99,780 per Acre

    5 Acres Lincoln Rd, Oregon, WI 53575

    Opportunity awaits on this 5 acre property just south of Madison in the Town of Oregon. Several outbuildings on the property including the original barn, 3 car detached garage and two pole sheds provide multiple possibilities for storage, hobbies or animals. Includes a Foursquare farm house. House and some outbuildings are in need of some TLC. Property is also listed as Single Family. Seller is

    Agent Photo

    Tommy Van Ess

    First Weber Inc

    5 Acres Lincoln Rd, Oregon, WI 53575
  • 187 Sterling Dr, Oregon, WI 53575
    187 Sterling Dr, Oregon, WI 53575
    187 Sterling Dr, Oregon, WI 53575
    /27

    $414,900

    $5K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,613 Sq Ft

    187 Sterling Dr, Oregon, WI 53575

    Beautiful ranch home offering the perfect blend of comfort, convenience, and outdoor enjoyment. Stunning hardwood floors welcome you inside, while the remodeled kitchen is ready for everyday living and entertaining alike. Unwind in the spa-like bathroom, designed to feel like your own private retreat. Outside, enjoy a generous lot featuring cherry trees, apple trees, plum tree, raspberry bush,

    Jason Fowler Century 21 Affiliated

    187 Sterling Dr, Oregon, WI 53575
  • 1206 Tivoli Cir, Oregon, WI 53575
    1206 Tivoli Cir, Oregon, WI 53575
    1206 Tivoli Cir, Oregon, WI 53575
    /32

    $420,000

    $30K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,292 Sq Ft

    1206 Tivoli Cir, Oregon, WI 53575

    Thoughtfully updated condo that truly lives like a single-family home in a welcoming Oregon community! Condo Fees are $200/month. Enjoy a private entry and convenient 2-car attached garage, along with vaulted ceilings and abundant natural light throughout the inviting main living space. Upgraded lighting, new flooring, and an enhanced kitchen with added pantry cabinetry and butcher block counter

    Matt Winzenried Realty Executives Cooper Spransy

    1206 Tivoli Cir, Oregon, WI 53575
  • + - 37 5ac County Rd A, Oregon, WI 53575
    + - 37 5ac County Rd A, Oregon, WI 53575
    + - 37 5ac County Rd A, Oregon, WI 53575
    /4

    $375,000

    • Land
    • 37.5 Acres
    • $10,000 per Acre

    + - 37 5ac County Rd A, Oregon, WI 53575

    A rare opportunity to secure 37.5 acres of productive tillable ground just outside Oregon, WI in the Town of Rutland. This high, rolling acreage offers excellent drainage, strong yield potential and easy access off County Rd A with quick connection to HWY 14. Its proximity to town makes it an exceptional piece of income-producing farmland. Ideal for operators looking to expand their tillable

    Al Weber First Weber Inc

    + - 37 5ac County Rd A, Oregon, WI 53575
  • 358 Alpine Meadow Cir, Oregon, WI 53575
    358 Alpine Meadow Cir, Oregon, WI 53575
    358 Alpine Meadow Cir, Oregon, WI 53575
    /22

    $300,000

    • 2 Beds
    • 2 Baths
    • 1,308 Sq Ft

    358 Alpine Meadow Cir, Oregon, WI 53575

    Rare find! This 2-bedroom, 2-bath ranch condo offers easy one level living with vaulted ceilings, beautiful lvp floors, and a comfortable open feel with lots of natural light. The kitchen features brand-new appliances in 2026, along with an impressive list of recent updates including a new washer an dryer in 2025, furnace, A/C and water heater in 2024, and new roof in 2022. The spacious

    Jo Ferraro EXP Realty, LLC

    358 Alpine Meadow Cir, Oregon, WI 53575
  • 956 Merri-Hill Dr Unit 36450832, Oregon, WI 53575
    956 Merri-Hill Dr Unit 36450832, Oregon, WI 53575
    956 Merri-Hill Dr Unit 36450832, Oregon, WI 53575
    /26

    $452,600

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,860 Sq Ft

    The Costello Plan at Greenview Preserve, Oregon, WI 53575

    WORK FROM HOME? NO PROBLEM HERE. With its spacious flex room, The Costello offers up the sanctuary you need to balance business with pleasure. Skip the fast food and prep your own gourmet lunch, because why wouldn’t you when you have a lovely kitchen pantry to hold all your meticulously organized spices and grains. When you’re ready to call it a day, retreat and recharge in your private oasis

    Veridian Homes Builder
    956 Merri-Hill Dr Unit 36450832, Oregon, WI 53575
  • 956 Merri-Hill Dr Unit 39223581, Oregon, WI 53575
    956 Merri-Hill Dr Unit 39223581, Oregon, WI 53575
    /2

    $439,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,528 Sq Ft

    The Chelsea Plan at Greenview Preserve, Oregon, WI 53575

    Every home tells a story — and The Chelsea was designed to begin a beautiful one. This two-story carriage lane home strikes a beautiful balance between charm and contemporary living. Step inside to an open, airy main floor that invites connection. From simple weeknight dinners to lively gatherings, this inviting layout makes every moment feel natural. Graceful yet grounded, The Chelsea feels both

    Veridian Homes Builder
    956 Merri-Hill Dr Unit 39223581, Oregon, WI 53575
  • 145 Dewey St, Oregon, WI 53575
    145 Dewey St, Oregon, WI 53575
    145 Dewey St, Oregon, WI 53575
    /56

    $429,900

    $5K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,410 Sq Ft

    145 Dewey St, Oregon, WI 53575

    If you're looking for a beautiful blend of yesteryear charm & modern updates, don't miss this Oregon charmer! Gorgeous woodwork, stained glass, exposed brick and hardwood floors create a warm, memorable space. An updated kitchen is the true heart of the home and is as functional as it is inviting - with room to gather, tons of counter space & storage (don't miss the huge pantry!). Two large

    Andrea Bolan Relish Realty

    145 Dewey St, Oregon, WI 53575
  • 1043 Merri Hill Dr, Oregon, WI 53575
    1043 Merri Hill Dr, Oregon, WI 53575
    1043 Merri Hill Dr, Oregon, WI 53575
    /16

    $394,900

    New Construction $5K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,481 Sq Ft

    1043 Merri Hill Dr, Oregon, WI 53575

    Renderings are for illustrative purposes only. Final colors, finishes, and landscaping will differ.All prices, promotions and specifications are subject to change at any time without notice based on the discretion of Veridian Homes.

    Veridian Homes Builder
    1043 Merri Hill Dr, Oregon, WI 53575
  • 1035 Merri Hill Dr, Oregon, WI 53575
    1035 Merri Hill Dr, Oregon, WI 53575
    1035 Merri Hill Dr, Oregon, WI 53575
    /15

    $424,900

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,511 Sq Ft

    1035 Merri Hill Dr, Oregon, WI 53575

    Renderings are for illustrative purposes only. Final colors, finishes, and landscaping will differ.All prices, promotions and specifications are subject to change at any time without notice based on the discretion of Veridian Homes.

    Veridian Homes Builder
    1035 Merri Hill Dr, Oregon, WI 53575
  • 1232 Tivoli Cir, Oregon, WI 53575
    1232 Tivoli Cir, Oregon, WI 53575
    1232 Tivoli Cir, Oregon, WI 53575
    /34

    $434,900

    • 2 Beds
    • 2 Baths
    • 1,292 Sq Ft

    1232 Tivoli Cir, Oregon, WI 53575

    The Villas are the ultimate in peace of mind living. Located within the Highlands of Netherwood, this unique neighborhood of Single Family homes brings all the conveniences of condo living (Fee: $200/mo) right to your door. Never mow your lawn or shovel your driveway again. Ideal for people that frequently travel or are in the area for part of the year. Walking path connects the neighborhood to a

    Jim Lampe Keller Williams Realty Signature

    1232 Tivoli Cir, Oregon, WI 53575
  • 456 New Hampton Dr, Oregon, WI 53575
    456 New Hampton Dr, Oregon, WI 53575
    456 New Hampton Dr, Oregon, WI 53575
    /15

    $464,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,615 Sq Ft

    456 New Hampton Dr, Oregon, WI 53575

    Renderings are for illustrative purposes only. Final colors, finishes, and landscaping will differ.All prices, promotions and specifications are subject to change at any time without notice based on the discretion of Veridian Homes.

    Veridian Homes Builder
    456 New Hampton Dr, Oregon, WI 53575
  • 456 Savannah Dr, Oregon, WI 53575
    456 Savannah Dr, Oregon, WI 53575
    /2

    $429,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,525 Sq Ft

    456 Savannah Dr, Oregon, WI 53575

    Renderings are for illustrative purposes only. Final colors, finishes, and landscaping will differ.All prices, promotions and specifications are subject to change at any time without notice based on the discretion of Veridian Homes.

    Veridian Homes Builder
    456 Savannah Dr, Oregon, WI 53575
  • 956 Merri-Hill Dr Unit 40971249, Oregon, WI 53575
    956 Merri-Hill Dr Unit 40971249, Oregon, WI 53575
    956 Merri-Hill Dr Unit 40971249, Oregon, WI 53575
    /42

    $493,600

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,572 Sq Ft

    The Harlow Plan at Greenview Preserve, Oregon, WI 53575

    One look at the primary suite in The Harlow and you’ll feel your pulse quicken... an inviting retreat with a private bath and a closet spacious enough to dance in. The kitchen steals the show with a generous island perfect for entertaining, paired with a sunny set of patio doors that welcome in morning light for a quiet cup of coffee before the day begins. This thoughtfully designed single-level

    Veridian Homes Builder
    956 Merri-Hill Dr Unit 40971249, Oregon, WI 53575
  • 956 Merri-Hill Dr Unit 36789044, Oregon, WI 53575
    956 Merri-Hill Dr Unit 36789044, Oregon, WI 53575
    956 Merri-Hill Dr Unit 36789044, Oregon, WI 53575
    /17

    $427,500

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,615 Sq Ft

    The Gramercy Plan at Greenview Preserve, Oregon, WI 53575

    Your takeout never tasted so good. No, it wasn’t that the food was any different, it was where it was eaten. That’s right, you ate at the best location around, at your brand new kitchen island. The experience that the Gramercy has to offer you is like it was made just for you (because it was!). With an open and airy first floor and three private retreats upstairs, you are exactly where you should

    Veridian Homes Builder
    956 Merri-Hill Dr Unit 36789044, Oregon, WI 53575
  • 828 Dunn Ave, Oregon, WI 53575
    828 Dunn Ave, Oregon, WI 53575
    828 Dunn Ave, Oregon, WI 53575
    /30

    $384,000

    $32K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,790 Sq Ft

    828 Dunn Ave, Oregon, WI 53575

    Must-see 3BR Ranch-style condo with updates and flexible living space! Main level features newer granite counters, appliances & flooring, gas fireplace, primary suite, laundry & 1/2 bath. Exposed lower level offers 2 bedrooms, full bath, spacious family room that could serve as a 4th bedroom, plus ample storage. New roof & siding in 2026. Newer deck off dining area. Ideally located close to

    Lori Zander Century 21 Affiliated Roessler

    828 Dunn Ave, Oregon, WI 53575
  • 326 Alpine Meadow Cir, Oregon, WI 53575
    326 Alpine Meadow Cir, Oregon, WI 53575
    326 Alpine Meadow Cir, Oregon, WI 53575
    /16

    $299,900

    • 2 Beds
    • 2.5 Baths
    • 1,464 Sq Ft

    326 Alpine Meadow Cir, Oregon, WI 53575

    This inviting townhome offers spacious bedrooms, a generously sized primary suite, and the comfort of a full primary bath. The home has recently been refreshed with all-new flooring, giving the interior a clean, updated feel.The two oversized bedrooms provide plenty of room for furniture, guests, a home office, or additional living space, while the large primary suite offers a comfortable retreat

    Noel Barnes Barnes & Associates Realty Group

    326 Alpine Meadow Cir, Oregon, WI 53575
  • 956 Merri-Hill Dr Unit 36788946, Oregon, WI 53575
    956 Merri-Hill Dr Unit 36788946, Oregon, WI 53575
    956 Merri-Hill Dr Unit 36788946, Oregon, WI 53575
    /3

    $415,500

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,525 Sq Ft

    The Tribeca Plan at Greenview Preserve, Oregon, WI 53575

    Eggs sunny side up, at the sunniest breakfast nook around. Your breakfast nook. Yes, even the coffee tastes better while sipped slowly on the sofa that is anchoring your spacious great room. Why don’t you head on upstairs and grab the coziest robe you can find from your walk-in closet and then enjoy a quick read of the newspaper while out on your front porch. Because this really is all yours.

    Veridian Homes Builder
    956 Merri-Hill Dr Unit 36788946, Oregon, WI 53575
  • Lot Borchert Rd, Oregon, WI 53575
    Lot Borchert Rd, Oregon, WI 53575
    Lot Borchert Rd, Oregon, WI 53575
    /7

    $275,000

    • Land
    • 1.69 Acres
    • $162,722 per Acre

    Lot Borchert Rd, Oregon, WI 53575

    Schedule a showing to walk the lot. Beautiful 1.69-acre wooded lot in the City of Fitchburg offering the rare opportunity to build your peaceful dream home with a country feel, yet just minutes from the conveniences of Madison. Nestled in a serene natural setting, this picturesque homesite provides the perfect backdrop for privacy, tranquility, and the custom home you’ve always envisioned.

    Kristine Jaeger Sprinkman Real Estate

    Lot Borchert Rd, Oregon, WI 53575
  • 1087 Tundra Ave, Oregon, WI 53575
    1087 Tundra Ave, Oregon, WI 53575
    1087 Tundra Ave, Oregon, WI 53575
    /14

    $399,900

    New Construction $15K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,848 Sq Ft

    1087 Tundra Ave, Oregon, WI 53575

    Renderings are for illustrative purposes only. Final colors, finishes, and landscaping will differ.All prices, promotions and specifications are subject to change at any time without notice based on the discretion of Veridian Homes.

    Veridian Homes Builder
    1087 Tundra Ave, Oregon, WI 53575
  • 329 Soden Dr, Oregon, WI 53575
    329 Soden Dr, Oregon, WI 53575
    329 Soden Dr, Oregon, WI 53575
    /48

    $319,900

    • 2 Beds
    • 1 Bath
    • 1,100 Sq Ft

    329 Soden Dr, Oregon, WI 53575

    Single-Level Comfort Meets Everyday Convenience. Enjoy the ease of single-level living in this welcoming 2-bedroom, 1-bath ranch-style duplex offering approximately 1,100 square feet of thoughtfully designed space. The open floor plan flows effortlessly from room to room, while a vaulted ceiling enhances the bright, spacious feel. Accessible features add everyday convenience, and a walk-in closet

    Matt Kornstedt Stark Company, REALTORS

    329 Soden Dr, Oregon, WI 53575
  • 462 New Hampton Dr, Oregon, WI 53575
    462 New Hampton Dr, Oregon, WI 53575
    /2

    $449,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,528 Sq Ft

    462 New Hampton Dr, Oregon, WI 53575

    Renderings are for illustrative purposes only. Final colors, finishes, and landscaping will differ.All prices, promotions and specifications are subject to change at any time without notice based on the discretion of Veridian Homes.

    Veridian Homes Builder
    462 New Hampton Dr, Oregon, WI 53575
  • 450 Ithaca Ct, Oregon, WI 53575
    450 Ithaca Ct, Oregon, WI 53575
    450 Ithaca Ct, Oregon, WI 53575
    /28

    $460,000

    • 3 Beds
    • 3 Baths
    • 1,960 Sq Ft

    450 Ithaca Ct, Oregon, WI 53575

    Built in 2020, this accessible ranch duplex in the Village of Oregon is within walking distance of the library and shopping and across the street from walking/biking trails. The main floor features a zero entry/no step in from the garage, an open concept floor plan with vaulted ceilings, and 2 bedrooms. The spacious lower level offers a large rec room, a 3rd bedroom, and plenty of storage. Catch

    Bryan Reichling EXP Realty, LLC

    450 Ithaca Ct, Oregon, WI 53575
  • 991 US Highway 14, Oregon, WI 53575
    991 US Highway 14, Oregon, WI 53575
    991 US Highway 14, Oregon, WI 53575
    /28

    $335,000

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft

    991 US Highway 14, Oregon, WI 53575

    Beautifully updated ranch on nearly half an acre just minutes south of Oregon! Enjoy the feel of country living while still being close to everything Oregon has to offer. This 2-bedroom, 1-bath home has seen extensive recent updates, including a brand-new kitchen and bathroom, new siding (2026), and a new roof (2025). Inside, you'll find two nicely sized bedrooms and a comfortable, functional

    Andrew Krenz RE/MAX Preferred

    991 US Highway 14, Oregon, WI 53575
  • 377 Concord Dr, Oregon, WI 53575
    377 Concord Dr, Oregon, WI 53575
    377 Concord Dr, Oregon, WI 53575
    /40

    $365,000

    • 2 Beds
    • 2 Baths
    • 1,406 Sq Ft

    377 Concord Dr, Oregon, WI 53575

    Well maintained sun-lit 2-bed/2-bath condo in the highly-rated Oregon School District featuring great space, wonderful views, and offers the perfect balance of comfort and convenience. The main living area boasts vaulted ceilings, oversized windows, a cozy gas fireplace, and walkout to the balcony deck overlooking the property. The kitchen has abundant cabinetry, a spacious island, and an

    Jason Holtman RE/MAX Preferred

    377 Concord Dr, Oregon, WI 53575
  • 749 County Road Mm, Oregon, WI 53575
    749 County Road Mm, Oregon, WI 53575
    749 County Road Mm, Oregon, WI 53575
    /44

    $500,000

    • 3 Beds
    • 1 Bath
    • 1,179 Sq Ft

    749 County Road Mm, Oregon, WI 53575

    Inviting home on just under 4 acres within the top-rated Oregon School District, just 20 minutes from downtown Madison. The fantastic open layout creates an easy flow for entertaining, gathering with friends, and everyday living. You’ll love the character throughout, with original accents, exposed brick, gorgeous hardwood floors, and stylish finishes. Spend warm weather days on the patio taking

    Dan Chin Homes Team Real Broker LLC

    749 County Road Mm, Oregon, WI 53575
  • 956 Merri-Hill Dr Unit 36788978, Oregon, WI 53575

    $398,800

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,523 Sq Ft

    The Davis Twin Home Plan at Greenview Preserve - Twin Homes, Oregon, WI 53575

    WELL NOW THEY’VE THOUGHT OF EVERYTHING. That’s what you’ll be saying to yourself when you start settling into the Davis. With its six closets AND a pantry, you have all the room you need to store whatever your heart desires. So whether you’re a fashion enthusiast, an at home chef extraordinaire, or maybe you just have a lot of toys that need storing, the Davis lets you tuck away all your goodies.

    Veridian Homes Builder
    956 Merri-Hill Dr Unit 36788978, Oregon, WI 53575
  • 457 Savannah Dr, Oregon, WI 53575
    457 Savannah Dr, Oregon, WI 53575
    /2

    $429,900

    New Construction $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,528 Sq Ft

    457 Savannah Dr, Oregon, WI 53575

    Renderings are for illustrative purposes only. Final colors, finishes, and landscaping will differ.All prices, promotions and specifications are subject to change at any time without notice based on the discretion of Veridian Homes.

    Veridian Homes Builder
    457 Savannah Dr, Oregon, WI 53575
Wisconsin Dane County

Real Estate & Homes in Oregon, WI under $500,000

Home Prices in Oregon, WI

The median home sale price in Oregon, WI is $494,900, up 5% year-over-year. Homes in Oregon sell in 46 days on average, compared to the national average of 55 days.

Home Price Trends

Median Sale Price
$494,900
Median Single Family Sale Price
$480,604
Median 2 Bedroom Sale Price
$305,000
Average Price Per Sq Ft
$248
Number of Homes for Sale
29
Last 12 months Home Sales
247
Months of Supply
1.70
Median List Price
$483,054
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
5%
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